You can go on either side of the Elizabethan Islands. You can even go half way up Buzzards Bay and out into Vineyard Sound via Quicks or Robinson's hole. Check the currents and the conditions because going up Vineyard Sound against the currents can be slow and Buzzards Bay can be rough. If both are in your favor, pick your route and stops. Some options are Block Island, Newport, Cuttyhunk, Menemsha, Tarpaulin Cove, Hadley's Harbor, Vineyard Haven, Edgartown and Hyannis. Given that trip, you have so many options. It should take about 18-25 hours door to door depending on conditions, size of boat, etc. Have fun, it should be a nice trip.